Formaldehyde → HCID 18695619, compound

HRID 1586458Notes

Reaction equation

HRID 1586458 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][CH3:22])[N:12]=2)=[O:10])[CH2:4][CH2:3]1.[CH2:23]=O>C(O)=O>[CH3:23][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][CH3:22])[N:12]=2)=[O:10])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 712Formaldehyde2×HCID 69945232HCID 69945232, compound

Product 1

HCID 18695619HCID 18695619, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

To N-(4-piperidyl)-1-n-propylindazole-3-carboxamide hydrochloride (0.32 g) obtained in Example 20 were added formic acid (0.7 ml) and a 36% aqueous solution of formaldehyde (0.3 ml), and the mixture was stirred at room temperature for 5 hours. Then formic acid (4 ml) and a 36% aqueous solution of formaldehyde (1.6 ml) were further added, and the mixture was heated under reflux for 2.5 hours. The reaction solution was distilled off under reduced pressure, and to the residue were added chloroform and aqueous ammonia. After extraction with chloroform, the chloroform layer was washed with saturated aqueous sodium chloride, dried over anhydrous potassium carbonate, and distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform methanol:aqueous ammonia 90:10:2) to give the title compound (0.06 g). Yield 18%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. distillationThe reaction solution was distilled off under reduced pressure
  4. additionto the residue were added chloroform and aqueous ammonia
  5. extractionAfter extraction with chloroform
  6. washthe chloroform layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous potassium carbonate
  8. distillationdistilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (chloroform methanol:aqueous ammonia 90:10:2)

Sources & evidence

ORD record
ord-4fb0ea0bcc974b5fb0430643e00b8c21
Source dataset
uspto-grants-1999_08
Patent number
US05945434

Reaction notes

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